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Search results; Over 1,000 homes in Madison

Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
25–30 Aug
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4.98 out of 5 average rating, 226 reviews
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
17–22 Aug
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
4.98 out of 5 average rating, 87 reviews, 7 bedrooms, 13 beds, 5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Place to stay in Cambridge
Wye Three Oaks
4.96 out of 5 average rating, 101 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
4.96 out of 5 average rating, 74 reviews, 5 bedrooms, 5 beds, 2 bathrooms
6–11 Aug
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
5.0 out of 5 average rating, 247 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
4.94 out of 5 average rating, 188 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
4.99 out of 5 average rating, 219 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
4.99 out of 5 average rating, 142 reviews, 6 bedrooms, 11 beds, 4.5 bathrooms
5–10 Sept
Top guest favourite
Home in Madison
Madison Bay Club House
5.0 out of 5 average rating, 51 reviews, 3 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5.0 out of 5 average rating, 11 reviews, 5 bedrooms, 10 beds, 6 bathrooms
1–8 Aug
Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
5.0 out of 5 average rating, 42 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Aug
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
4.97 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Cambridge
Choptank Riverside Retreat
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Superhost
Home in Woolford
The Blue Heron-Spacious Waterfront house w/ kayaks
4.67 out of 5 average rating, 58 reviews, 6 bedrooms, 10 beds, 4 bathrooms
16–21 Aug
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Cambridge
Chesapeake Sunset Retreat
4.83 out of 5 average rating, 35 reviews, 4 bedrooms, 5 beds, 1.5 bathrooms
8–13 Sept
Top guest favourite
Home in Cambridge
Great Historic Cambridge Home With Parking!
4.95 out of 5 average rating, 280 reviews, 4 bedrooms, 7 beds, 3.5 bathrooms
3–8 Aug
Guest favourite
Home in Cambridge
Modern Chesapeake Waterfront - Heated Pool - Dock
5.0 out of 5 average rating, 9 reviews, 5 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept